This paper aims at analysing the concept of masculinity which has been under the feminists’ constant “attacks” for decades. Yet, we wanted to show how a male author depicted a type of ‘effeminate’ masculinity which stole its way into the Victorian society – the most rigid cultural epoch in history. We chose to discuss masculinity in Vanity Fair where Rebecca Sharp permanently attempts at subverting not only the gender roles, but also other well established Victorian binary oppositions: margin vs. centre, master vs. servant, appearance vs. reality. One of the effects of the woman’s subversion of male power/ authority is the emergence of dandies, who, despite their elegance and self-made persona, were heavily criticised by Thomas Carlyle or Honore de Balzac who defined them as “clothes-wearing men” – a feature normally attributed to women. Our survey on masculinity ranges from feminist theories to various definitions of masculinity studies or the male sex role identity paradigm, finally concentrating on the relation between femininity and masculinity in William Thackeray’s novel. One important aspect of our paper refers to narcissism and the defence mechanisms (such as sublimation, projection, introjection) present in the male characters from Vanity Fair, which reinforce the idea that a childhood/adolescence trauma can transform later into personality disorders. Thackeray’s representation of masculinity intends to oppose the Victorians’ perceptions about this concept and attempts at reversing the traditional gender roles.